I had hooked up with this guy before, for a while he was one of my regulars, gay, white, working class, used to be in the army, in his 40’s, big tall guy, I wanna say more than 6 feet, 200 something lbs, big and strong, a bears build but with incredibly smooth skin. He has a stunningly beautiful face, just striking, like when he was younger he was one of those shirtless boys on the cover of gay mags, however he looks and dresses like the guy next door mowing his lawn on weekends - Bermuda style shorts, short sleeve button up that stretches over his belly, flip flops.
He’s also a real sweetie. I love big burly ultra masculine guys who are sweethearts.
He sent me a text earlier in the week where he said he wanted to tell me something but didn’t know how to say it in a respectful way (I’m his first trans guy) to which I said just say it no worries. So he said in his entire lifetime he’s only had sex with two women before me or something to that effect… I can feel everyone cringing as you read this, however like I said he’s a total sweet heart and I know he respects my gender, I can tell he’s just struggling with words. So I just say well you know I’m a guy… he said yeah, of course, so I say each trans guy is different but for me you can say I’m only the third pussy you’ve ever fucked unless that’s too crude for you... Then he actually repeats it back to me via text – third pussy I’ve fucked. Totally made me smile. Very teachable.
Anyways onto the fucking cuz that's what this piece is really about.
So I get to his place and he starts kissing me as soon as i walk through the door. I can feel his hard on through his shorts, I'm very turned on. However, he wants to take a shower before we fuck so I decide to join him. His shower is real old school where there is just a shower head and drain in the floor of the bathroom – no stall or tub. This set up makes it extra hot, I’ve never been in a bathhouse but its what I imagine one would be like. We play around some, soaping each other up, I suck him off a bit, then this huge guy, kneels down before me on the old white tile floor and sucks me off, I place my hand on his head as he blows me – shower blow jobs – very hot. We dry off and head to his room.
He lies down on the bed and I climb on top of him, i say climb because that's how big he is. We kiss for a long time – he is an incredible kisser. He flips me over and sucks my nipples then tongues my clit for a while until its too much and I push him off. I put his cock in my mouth, he is already hard as I wrap my lips around his dick, he has a beautiful cock and I go at him for a bit, taking him down my throat, he groans.
He pulls me off and grabs a condom, I lube him up. He lies back and lifts me on top of him, I guide him into me, he's big and thick so i have to go slow at first, just the head until I can take more, he moans as my cunt finally fully encases his cock, I ride him for a while loving the look of pleasure on his face, then he turns me over, fucks me for a while in a couple different position until he lays me on my back puts my legs on his shoulders and as he's stroking says he's gonna cum, I tell him 'cum for me baby' and he starts pounding his full weight into me, until finally he shoots cumming inside me. so hot.
All the while we are fucking he keeps saying how amazing and sexy I am.
We rest for a bit, curled up together, he's a great cuddler. We chat some about our lives, then he starts talking politics, this is when i wish he would stop talking, he's a total conservative. I quickly change the subject - i'm here cuz you're a sweetie and amazing in bed - I don't want to get into your problematic political views.... thankfully, we talk about other random things then he kisses me and i can feel that he's hard again.
He begins fingering my nipples then put his lips around one, sucking until its erect, all the while he's playing with my clit, i moan wanting him badly, he says i just want to make you feel good. i tell him to get a condom and I pull him on top of me. He slowly pushes into me, then begins fucking me missionary style. He fucks me like this for a while and he's stroking me just right... in that way where his cock is filling me up and his body is rubbing my clit just hard enough. I’m glad no one else is home because between the banging of the bed and both of our moans we are being very loud.
He fucks me like this for a long time, our bodies pressed closely together and I can feel that i'm getting close to cumming, i wrap my arms around him, well as far as they'll go, and say into his ear 'don't stop'. he keeps going, stroking me harder and grinding his body against my clit and i'm losing it at this point, i'm raising my hips to meet each stroke, our fucking is frantic, i just keep saying 'don't stop' and he doesn't, as I start to cum his cock plunging deep inside me I hold him even tighter until my body literally explodes, i don't even know what i'm doing as i simultaneously clutch at him and push him away, one of the most incredible orgasms i've ever had.
He’s still fucking me and I can’t take it anymore, i tell him to stop, he stops immediately and looks at me concerned asks if I’m ok, if he hurt me, I shake my head and smile, ‘no man that was amazing’, funny thing about alot of gay boys they have no idea when your cumming. Anyways, he’s still hard, asks if i need to rest, and I do, but i want him to cum too so i shake my head turn around and he fucks me doggy style, its starting to be too much again and i'm about to tell him i can't anymore when he groans and collapses on top of me.
We lie like that for a while, then i move out from under him and put my head on his chest and we just rest.
Then i have to go. As i'm heading out the door I kiss him goodbye and he says please text me so i know you got home safe. I say you're such a sweetie. to which he says, "well we have to look out for each other because no one else will". bad politics and all I can't help but like this guy.